Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N 1,N 4,N 8,N 11)copper(II) didodeca­noate dihydrate

Nur Syamimi Ahmad Tajidi; Norbani Abdullah; Zainudin Arifin

doi:10.1107/S1600536811012773

. 2011 Apr 13;67(Pt 5):m588–m589. doi: 10.1107/S1600536811012773

Diaqua(1,4,8,11-tetraazacyclotetradecane-κ⁴ N ¹,N ⁴,N ⁸,N ¹¹)copper(II) didodecanoate dihydrate

Nur Syamimi Ahmad Tajidi ^a, Norbani Abdullah ^a,^*, Zainudin Arifin ^a

PMCID: PMC3089101 PMID: 21754311

Abstract

The title compound, [Cu(C₁₀H₂₄N₄)(H₂O)₂][CH₃(CH₂)₁₀CO₂]₂·2H₂O, consists of one cationic copper(II) complex, two dodecanoate anions and two water solvent molecules. The Cu^II atom is located on an inversion center and is chelated by the four aza N atoms of the neutral 1,4,8,11-tetraazacyclotetradecane (cyclam) ligand and by two water molecules in axial positions, giving an octahedral coordination geometry, distorted as a consequence of the Jahn–Teller effect. The uncoordinated water molecules link the complex cations and the dodecanoate counter-ions through O—H⋯O hydrogen bonding, forming a layer structure parallel to (001). Intermolecular N—H⋯O interactions also occur.

Related literature

For the complexation of cyclam with transition metals, see: Ahmad Tajidi et al. (2010a ▶,b ▶,c ▶,d ▶); Lindoy et al. (2003 ▶); Holanda et al. (2007 ▶); Sreedaran et al. (2008 ▶); Zgolli et al. (2010 ▶).

Experimental

Crystal data

[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₁₂H₂₃O₂)₂·2H₂O
M _r = 734.54
Triclinic,
a = 6.9972 (4) Å
b = 8.8164 (5) Å
c = 17.1495 (10) Å
α = 96.218 (3)°
β = 99.137 (3)°
γ = 98.329 (3)°
V = 1024.13 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 150 K
0.41 × 0.41 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.796, T _max = 0.955
7085 measured reflections
4623 independent reflections
4138 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.129
S = 1.07
4623 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012773/dn2672sup1.cif

e-67-0m588-sup1.cif^{(29.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012773/dn2672Isup2.hkl

e-67-0m588-Isup2.hkl^{(226.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O2	0.90	1.91	2.774 (2)	160
O1W—H1WA⋯O2ⁱ	0.90	1.81	2.694 (2)	168
O2W—H2WB⋯O1W	0.90	1.93	2.8037 (19)	164
O2W—H2WA⋯O1ⁱⁱ	0.90	1.89	2.777 (2)	168
N2—H2⋯O1ⁱ	0.93	2.25	3.030 (2)	141
N1—H1⋯O1Wⁱⁱⁱ	0.93	2.12	2.982 (2)	153

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This project was financed by the University of Malaya (grant No. A-50101-DA000-B21519). The authors thank Mr Harry Adams for his support and cooperation.

supplementary crystallographic information

Comment

Copper(II) cyclam complexes are potential functional materials in the field of molecular electronic, photonics and spintronics whose properties may be tuned by steric and electronic effects. The present complex represents our attempt to synthesize a functional material that possesses metallomesogenic properties for such applications. Several cyclam complexes with copper(II) (Ahmad Tajidi et al., 2010a,b,c,d) and other transition metals (Lindoy et al., 2003; Holanda et al., 2007; Sreedaran et al., 2008; Zgolli et al., 2010) have been reported.

In the complex, the Cu^II atom, located on an inversion center, is coordinated to the 1,4,8,11-tetraazacyclotetradecane through the four aza-N atoms forming the basal plane of a distorted octahedra whose apices are occupy by two water molecules. Two solvate water molecules link anion and cations through O-H···O hydrogen bondings (Fig. 1, Table 1). The relatively long Cu-O(water) distance, 2.455 (1)Å, is a consequence of the Jahn-Teller effect resulting in the distorted octahedron coordination geometry.

O-H···O and N-H···O Hydrogen bonds involving the coordinated and non coordinated water molecules, the carboxylate O atoms as well as the N atoms of the cyclam build up a two dimensionnal network forming a layer parallel to the (0 0 1) plane (Table 1, Fig. 2).

Experimental

An ethanolic solution of cyclam (2.50 mmol, 50 ml) was added to a warm ethanolic solution of dimeric copper(II) dodecanoate (1.25 mmol, 100 ml), forming a clear purple solution. The solution was then gently heated for 2 h. Purple plates formed upon cooling to room temperature. The yield was 60%.